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Allison Winn Scotch Headshot

What If?

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FINANCIAL MISTAKES

Recently, I got an email from a reader - a deeply personal email sharing "how she was questioning her marriage, thinking about an old boyfriend, wondering what would have happened with him if she'd hadn't gotten married." Her note resonated long after I'd written her back, thanking her for her kind words about my books. Receiving emails from readers isn't that unusual, so I can't say why I lingered on this one, but hours -- and then days -- later, I was still considering what she'd written. And, at the risk of sounding like Carrie Bradshaw, what I was still considering was this:

In an era when women try to have it all, why are so many of us left wondering about the road -- and often, the man -- not taken? Let's face it: we're the have-it-all generation. We work hard, we raise our kids confidently, we're entitled to good sex, we tackle five-mile jogs three times a week. And yet, whenever women in my demographic hear the premises of my books -- premises that explore our what-ifs about old loves, old lives, old portions of ourselves -- nearly all of these women slide up to me and say, "Ooooh yes, I get that entirely." And then they whisper their secrets to me -- or send me an email or a tweet -- about how their husbands make them crazy or how they spent an hour the previous evening stalking their college boyfriend online.

So just why is it that we seem to have it all and yet wish that we had it all differently?

My own what-ifs first arose at 26, when I was listless in the way that my characters are: determined but unpinned, smart but unfocused, grounded and yet lost. I was embroiled in a doomed relationship that I couldn't slice myself free from; I was trying on different career hats like they were disposable. I found myself in Los Angeles, single but still tangled up with that man who I loved but was wrong for me, pursued by another man who I didn't love but who I dated because I was too tired to protest, and faced with those unavoidable questions: What now? What if? What if I can find someone else to love? What if I can't? What if I can finally figure out what to do with my life?

Eventually, I took small steps toward finding the answers. I moved back to New York, where my friends and family provided a cushion. I started writing professionally, which was incredibly gratifying and gave me the confidence to make bolder moves in other areas of my life. Like breaking ties with the ex and upon seeing a cute boy in the gym, introducing myself and asking him out. A year later, that cute boy and I got engaged. And I stopped asking myself "what if" because there were fewer things to wonder about. By taking action, I was making them happen all on their own.

Still though, life comes in cycles, and even with all of that behind me -- even at 38, with nine years of marriage, two kids and a dog with a weak stomach -- I still ask what if? Facebook and Google make everyone -- everything -- so accessible. My grandmother -- and even my mother -- never had to worry about an old boyfriend popping up and asking to accept his friend request. We do. We're shown their relationship status, given access into their perfectly-witty status updates, and left to ponder over whether they occasionally peruse our relationship status and our perfectly-witty status updates as well. But blaming Facebook is just scape-goating the larger issue of our generation: that these longings for the road not taken exist in the first place. Though, if we really think about it, maybe these longings have always existed, maybe it's simply that we now have the portal -- email, Facebook, whatever -- to do something about them. Maybe our generation is just making our what ifs seem like something unfamiliar: divorce isn't taboo in the way that it once was. Marriage is more fluid than ever. What if? What if that one we'd left behind didn't have that habit of picking his toenails while we tried to watch a movie? What if, what if, what if!

After a few days, I wrote the reader back again. What I said was this: that no matter how successful we are, or how contented, these big questions will always trail us. That's life. That's human nature. That's the way it goes for women who came of age being told that we can have it all. We can have it all, some of the time. I remind myself of this every day-how much I love my husband, how blessed I am for my kids and my career and my full DVR and Chinese take-out. But all of this doesn't stop us from wondering what else there is to be had, and maybe that's okay. Maybe, by asking ourselves what if? we can also, at long last, ask ourselves, "what next?" And then, we can point ourselves toward the future, not just the past.

Allison Winn Scotch is the New York Times bestselling author of three novels, including THE ONE THAT I WANT (Crown) which is available this week in paperback. She can be found online at allisonwinn.com and on Twitter at @aswinn.